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• W2000345825 abstract "Abstract Proton nuclear magnetic resonance (nmr) spectra of d-biotin methyl ester (scheme 1) and its N-methoxycarbonyl derivative (scheme 2) were determined in CD3CN in the absence and presence of magnesium perchlorate or silver perchlorate In the metal-free spectrum of 2, the methylene protons of the tetrahydrothiophene ring appeared equivalently, suggesting a rapid flipping of the ring on the nmr time-scale. Addition of magnesium ion to 1 or 2 gave rise to a down-field shift of protons of varying degree. The hydrogens at the 3 and 4 position (H3 and H4) of the tetrahydrothiophene ring exhibited the largest shift, followed by the hydrogens at the 2 (H2) and 5 (H5) position. Similar experiments with silver ion gave opposite results, H2 and H5 underwent the larger shift. These data are interpreted as indicating that the magnesium ion interacts primarily with the ureido carbonyl. The lack of interaction between magnesium and the sulfide was verified by experiments with a biotin model compound carrying no sulfur atom. The significance of these results is discussed in connection with the possible involvement of a metal in the enolization of the ureido carbonyl of biotin." @default.
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• W2000345825 date "1984-06-01" @default.
• W2000345825 modified "2023-09-26" @default.
• W2000345825 title "Proton nmr study of metal coordination to biotin derivatives" @default.
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• W2000345825 doi "https://doi.org/10.1016/0162-0134(84)85042-4" @default.
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